Generation and electrophilic substitution reactions of 3-lithio-2-methyleneaziridines

Tetrahedron

Volumn 62, Issue 36, 2006, Pages 8447-8457

  Montagne, Cyril ^a   Prévost, Natacha ^b   Shiers, Jason J ^a   Prié, Gildas ^a   Rahman, Sabitur ^b   Hayes, Jerome F ^c   Shipman, Michael ^a  

^a UNIVERSITY OF WARWICK   (United Kingdom)

^b UNIVERSITY OF EXETER   (United Kingdom)

^c GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Aziridines; Organolithiums; Strained compounds

Indexed keywords

AZIRIDINE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHIRALITY; LITHIATION; PRIORITY JOURNAL; PROTON TRANSPORT; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 33746272004     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.06.083     Document Type: Article

References (32)

1. Prié G., Prévost N., Twin H., Fernandes S.A., Hayes J.F., and Shipman M. Angew. Chem., Int. Ed. 43 (2004) 6517-6519
2. Hayes J.F., Shipman M., and Twin H. Chem. Commun. (2000) 1791-1792
3. Hayes J.F., Shipman M., and Twin H. Chem. Commun. (2001) 1784-1785
4. Hayes J.F., Shipman M., and Twin H. J. Org. Chem. 67 (2002) 935-942
5. Hayes J.F., Shipman M., Slawin A.M.Z., and Twin H. Heterocycles 58 (2002) 243-250
6. Margathe J.F., Shipman M., and Smith S.C. Org. Lett. 7 (2005) 4987-4990
7. Shiers J.J., Clarkson G.J., Shipman M., and Hayes J.F. Chem. Commun. (2006) 649-651
8. Prévost N., and Shipman M. Org. Lett. 3 (2001) 2383-2385
9. Prévost N., and Shipman M. Tetrahedron 58 (2002) 7165-7175
10. Oh B.H., Nakamura I., and Yamamoto Y. Tetrahedron Lett. 43 (2002) 9625-9628
11. Oh Y.H., Nakamura I., and Yamamoto Y. J. Org. Chem. 69 (2004) 2856-2858
12. Siriwardana A.I., Kathriarachchi K., Nakamura I., Gridnev I.D., and Yamamoto Y. J. Am. Chem. Soc. 126 (2004) 13898-13899
13. Pollard C.B., and Parcell R.F. J. Am. Chem. Soc. 73 (1951) 2925-2927
14. For the correct structural assignments, see:. Ettlinger M.G., and Kennedy F. Chem. Ind. (1956) 166-167
15. Bottini A.T., and Roberts J.D. J. Am. Chem. Soc. 79 (1957) 1462-1464
16. Shiers J.J., Shipman M., Hayes J.F., and Slawin A.M.Z. J. Am. Chem. Soc. 126 (2004) 6868-6869 and references therein.
17. Bingham E.M., and Gilbert J.C. J. Org. Chem. 40 (1975) 224-228
18. Wijnberg J.B.P.A., Wiering P.G., and Steinberg H. Synthesis (1981) 901-903
19. De Kimpe N., DeSmaele D., and Sakonyi Z. J. Org. Chem. 62 (1997) 2448-2452
20. Tehrani K.A., and De Kimpe N. Tetrahedron Lett. 41 (2000) 1975-1978
21. Quast H., and Weise Vélez C.A. Angew. Chem., Int. Ed. Engl. 13 (1974) 342-343
22. Quast H., and Weise Vélez C.A. Angew. Chem., Int. Ed. Engl. 17 (1978) 213-214
23. For a preliminary account of part of this work, see:. Hayes J.F., Prévost N., Prokes I., Shipman M., Slawin A.M.Z., and Twin H. Chem. Commun. (2003) 1344-1345
24. Ennis D.S., Ince J., Rahman S., and Shipman M. J. Chem. Soc., Perkin Trans. 1 (2000) 2047-2053
25. Ince J., Ross T.M., Shipman M., Slawin A.M.Z., and Ennis D.S. Tetrahedron 52 (1996) 7037-7044
26. Quast H., and Risler W. Angew. Chem., Int. Ed. Engl. 12 (1973) 414-415
27. Skattebol L. Acta Chem. Scand. 17 (1963) 1683-1693 and references therein.
28. Borer M., and Neuenschwander M. Helv. Chim. Acta 80 (1997) 2486-2501
29. 2Br were obtained in low yield and poor enantioselectivity.
30. Juaristi E., León-Romo J.L., Reyes A., and Escalante J. Tetrahedron: Asymmetry 10 (1999) 2441-2495
31. These X-ray crystal structures were first reported elsewhere [(Z)-24 (Ref. 8); 39 (Ref. 11)]. These structures are available from the Cambridge Crystallographic Database [(Z)-24 (CCDC243138); 39 (CCDC207055)].
32. Reich H.J. J. Chem. Educ.: Software, Series D 3D (1996)